![](https://forever.travel-assets.com/flex/flexmanager/images/2020/11/06/TVLY-MSJE-DTG-Hero-Image.jpg?impolicy=fcrop&w=900&h=225&q=mediumHigh)
Deals on vacations and trips to Crestwood
Save when you book Crestwood package deals
Crestwood flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
![Sonesta Simply Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/330000/328600/328524/ddda760e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Sonesta Simply Suites Chicago O'Hare Airport
O'Hare
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests have free WiFi and a free airport shuttle. Traveling on business? Take advantage of the 2 conference rooms, along with the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/0a75f592_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Dry cleaning and a safe deposit box are also provided.
![Fairmont Chicago at Millennium Park Gold Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577141/223eec73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 10
found 7 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.
![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.
![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.
Top Crestwood hotels deals
![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/41255425_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
$161
per night
Jul 2 - Jul 3
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1676cf3d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $191 per night
$191
per night
Jul 1 - Jul 2
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/a97325e3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
River Hotel
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $171 per night
$171
per night
Jun 30 - Jul 1
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/5dc4c553_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $170 per night
$170
per night
Jul 10 - Jul 11
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Spa
Free WiFi
![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/f8a6a426_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $119 per night
$119
per night
Jun 30 - Jul 1
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Free WiFi
![InterContinental Chicago Magnificent Mile, an IHG Hotel](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/51496272_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
InterContinental Chicago Magnificent Mile, an IHG Hotel
505 N Michigan Ave, Chicago, IL
Free Cancellation
The price is $209 per night
$209
per night
Jul 11 - Jul 12
This historic hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. You'll appreciate the steam room, bar/lounge, and coffee shop.
Pool
Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Six Flags Great America
4.5/5(347 reviews)
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Photos of local treasures
Browse Crestwood vacation photos for more inspiration